Dicyclohexylcarbodiimide → HCID 71515463, Verbindung

HRID 1855213

Reaktionsgleichung

Reaktionsgleichung von HRID 1855213
[Cl:1][CH2:2][CH2:3][N:4]([CH2:15][CH2:16][Cl:17])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:33]([C:37]1[O:41][C:40]([CH2:42][S:43][C:44]2[S:48][C:47]([NH2:49])=[N:46][CH:45]=2)=[N:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:17][CH2:16][CH2:15][N:4]([CH2:3][CH2:2][Cl:1])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:49][C:47]2[S:48][C:44]([S:43][CH2:42][C:40]3[O:41][C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:38][N:39]=3)=[CH:45][N:46]=2)=[O:14])=[CH:9][CH:10]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 25306PhenacidHCID 110654845-(((5-(tert-Butyl)oxazol-2-yl)methyl)thio)thiazol-2-amine

Produkt 1

HCID 71515463HCID 71515463, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred methylene chloride solution (20 ml) was added DMAP (438 mg, 3.59 mmol) and 2-(4-(bis(2-chloroethyl)amino)phenyl)acetic acid (B-5) (906 mg, 3.27 mmol). Subsequently, DCC (690 mg, 3.35 mmol) was added to reaction mixture, followed by addition of 5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-amine (Intermediate CY-200) (800 mg, 2.97 mmol). The mixture was stirred at r.t for 24 h. After removing dicyclohexylurea (DCU) by filtration, the filtrate was concentrated in vacuum and dried over Na2SO4. The residue was purified by silica gel chromatography eluting with CH2Cl2: EtOAc=20:1 to afford total product (1.2 g, 76%) as a gray solid. LC-MS: (M+H)+=528. 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 7.28-7.30 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.69 (d, J=8.7 Hz, 2H), 6.58 (s, 1H), 3.95 (s, 2H), 363-3.79 (m, 10H), 1.26 (s, 9H).

Aufarbeitung

  1. customAfter removing dicyclohexylurea (DCU)
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuum
  4. dry with materialdried over Na2SO4
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-d7b30cf313d545548dbd3ad41ef646d1
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962855B2

Verknüpfte Notizen

Wird geladen…